An efficient one pot regioselective synthesis of a 3,3′-spiro-phosphonylpyrazole-oxindole framework via base mediated [1,3]-dipolar cycloaddition reaction of the Bestmann–Ohira reagent with methyleneindolinones

Shelke, Anil M.; Suryavanshi, Gurunath

doi:10.1039/c5ob01020a

Cited by 45 publications

(12 citation statements)

References 74 publications

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“…Compounds 13 40 and 14 41 were prepared according to literature. Spectroscopic data for compounds 1, 42 2, 43 3, 44 4, 45 5, 46 8, 47 9, 48 were in agreement with literature values.…”

Section: General Procedures For the Synthesis Of Compounds 10-12supporting

confidence: 89%

Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast

et al. 2017

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“…Compounds 13 40 and 14 41 were prepared according to literature. Spectroscopic data for compounds 1, 42 2, 43 3, 44 4, 45 5, 46 8, 47 9, 48 were in agreement with literature values.…”

Section: General Procedures For the Synthesis Of Compounds 10-12supporting

confidence: 89%

Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast

et al. 2017

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“…Contemporarily, Suryavanshi and co-workers also reported a base promoted 1,3-dipolar cycloaddition reaction of BOR with methyleneindolinones to obtain a diverse range of 3,3'spiro-phosphonylpyrazole-oxindoles in good yields. [21] Our continued efforts towards the synthesis of spiropyrazole based scaffolds prompted us to employ a variety of activated olefins for the 1,3-dipolar cycloaddition reaction with diazomethylphosphonate (DAMP) anion. Even though the Seyferth-Gilbert reagent has been extensively employed for the construction of phosphonylpyrazoles, the reports to access spiropyrazolines are quite scarce.…”

Section: Synthesis Of Pyrazolesmentioning

confidence: 99%

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Jamali

Vaishanv

Mohanan

2020

The Chemical Record

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Azaheterocycles are one of the most prevalent classes of compounds present in numerous bioactive compounds, natural products, and agrochemicals, and undoubtedly, new methods to access them are always in high demand. Among the methods available, the 1,3dipolar cycloaddition reactions involving diazo compounds are particularly attractive because of their ability to rapidly construct densely functionalized azaheterocycles in a regioselective manner. In this context, the Bestmann-Ohira reagent has become a well-known reagent for the 1,3dipolar cycloaddition reactions to produce phosphonylated heterocycles, besides its widespread use as a homologating agent for the conversion of aldehydes to alkynes. This account details our efforts toward broadening the synthetic utility of the Bestmann-Ohira reagent and related compounds for the preparation of azaheterocycles such as pyrazoles, spirooxindoles, triazoles, triazolines, and spiropyrazolines, emphasizing on domino multicomponent reactions employing readily available feedstock reagents.

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“…reported in 2015 a one‐pot highly regioselective 1,3‐dipolar cycloaddition reaction with BOR, giving a facile procedure to access racemic 3,3′‐spiro‐phosphonylpyrazole‐oxindoles. Conditions screening indicated that the use of KOH as base could promote the formation of 423 in generally good yields within only 10 min (Scheme ) . The mechanism might involve the initial cycloaddition of 422 and 412 to afford pyrazoline 424 .…”

Section: Reactions Involving Heterocyclic Ring Formationmentioning

confidence: 99%

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

2020

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Scheme 20. Phosphonation of pyridinones.Scheme 21. CuI-catalyzed phosphoramidate formation.Scheme22. Phosphonation of coumarin and quinolinone.Scheme23. Silver(I)-catalyzed phosphonation of coumarins. Scheme 33. Electrochemical C(sp 2 )ÀHphosphonation of quinoxaline-2(1H)-ones. Scheme 39. Phosphorylation of quinoxaline-2(1 H)-ones. Scheme40. Autoxidative phosphorylation of quinoxalines. Scheme 41. DTBP-mediated formation of phosphonated benzothiazoles. Scheme42. Phosphonation of imidazole[2,1-b]thiazoles.Scheme 47. Copper(I)-catalyzedp hosphonationo fN-iminoisoquinolinium ylides. Scheme48. Aerobic phosphonationofC ( sp 3 ) À Hbonds. Scheme 49. Copper(II)/PBQ-catalyzed phosphorylation of 3,4-dihydro-1,4-benzoxazin-2-ones. Scheme 87. Asymmetric exo-selective [3+ +2] cycloaddition to afford phosphorus-substituted pyrrolidines. Scheme 95. Cascade condensation/cyclization to phosphonylated thienopyridines. Scheme 96. S N Ar'-involved cascade reactions to phosphonylated oxygenorn itrogen heterocycles.Scheme 97. Manganese(III)-mediated synthesis of 3-phosphonyldihydrofuransfrom b-ketophosphonates.Scheme98. Cyclization to phosphonated isochromenes.Scheme 121. Asymmetric [4+ +2] cycloaddition of b,g-unsaturated a-ketophosphonates.

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An efficient one pot regioselective synthesis of a 3,3′-spiro-phosphonylpyrazole-oxindole framework via base mediated [1,3]-dipolar cycloaddition reaction of the Bestmann–Ohira reagent with methyleneindolinones

Cited by 45 publications

References 74 publications

Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast

Biocatalysed olefin reduction of 3-alkylidene oxindoles by baker's yeast

The Bestmann‐Ohira Reagent and Related Diazo Compounds for the Synthesis of Azaheterocycles

Recent Advances in the Construction of Phosphorus‐Substituted Heterocycles, 2009–2019

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